Behavior of 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)acrylamide towards some nitrogen nucleophiles

Abstract

The versatile, hitherto unreported 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)-acrylamide 2 was synthesized and allowed to react with hydroxylamine, hydrazine and guanidine to afford regioselectively the isoxazole 4, pyrazole 6 and pyrimidine 8 derivatives, respectively. The reaction of 2 with thiourea and / or ethyl glycinate in a basic medium afforded the regioisomeric pyrimidinethione 9 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 14. Compound 2 reacts also with 2-amino-4-phenylthiazole, 2-amino-4-methylpyridine, 2-aminotetrazole, 2-aminobenzothiazole and 2-aminobenzimidazole to give the corresponding bridgehead nitrogen heterocycles namely thiazolo

Chiral induction in a novel self-assembled supramolecular system composed of α-cyclodextrin porous liquids, chiral silver nanoparticles and planar conjugated molecules

“…Fig. S1 (ESI †) exhibits the 1 singlet signal at 10.55 ppm assigned to the (-NH) proton of the amide group 40 and multiplet signals at 6.13-7.91 ppm owing to aromatic protons in the azobenzene group were found, which indicates that the azophenyl group is bonded to Ag NPs. A peak at 7.11 ppm belonging to aromatic protons in the azobenzene group and one peak located at 3.38 ppm associated with methylene in S-CH 2 -CH were also observed.…”

Recent synthetic methodologies for pyrimidine and its derivatives

“…Similarly, thiazoles linked with various heterocycles via carboxamide linkage are found to possess remarkable medicinal activities. Bondock and coworkers synthesized 2,4-diamino-N -(4-phenylthiazole-2-yl)pyrimidine-5-carboxamide 189 by the reaction of enaminonitrile 188 with guanidine hydrochloride 50 (Scheme 54) 80.…”